The unofficial rule of thumb for frequent towing is to not exceed 80% of the rated capacity to ensure longer term reliability and ensure decent performance braking and maneuvering the load. So, ideally you should be looking for something rated for 6k+. If you're just towing around town once every couple of weeks or so the vehicles you mentioned would probably do fine. If you're towing weekly for any sort of mileage you'd probably be happier and safer (you and the drivetrain) with something of the 1/2 ton variety.

I think you could find a kinda high mileage 8-10 year old Tahoe/Yukon or Expedition for about $5k. I passed on a pristine 150,000 mile '03 Tahoe w/ the 5.3L for $4,700 about a year and a half ago because I really wanted a pickup. Probably should have bought it anyway. They're out there you just have to be patient and maybe work the deal over time if the price is a little out of reach.

How far is your drive to the ramp? Whatt kind of incline/elavation are you at? Don't sacrifice safety for a cheap tow vehicle if you have a long haul. That being said I tow with a 2005 V8 Toyota 4Runner that I picked up for a good deal and it trailers my Sanger likena champ. Tough to answer your question without knowing what your tow conditions are.

a 4runner would work well, i had an 04 4runner and towed my bu vride with a dual axle trailer for 3 years. no problems and i tow 100miles each weekend. I am not sure what price point is out there, but you could find a high milage 4runner in the 5 ot 8k range good luck

You can find mid to late 90's Tahoe/Yukons for that range I think. They will all have over 100k but I think they are fairly simple and cheap to work on. Might also be able to find a late 90's expedition. I had a 99 Eddie Bauer and it was a nice rig. Got terrible gas mileage but was a good rig. Do you have any big hills to either ramp? Any highways or is it all surface streets?

You'll spend a lot fixing the trailblazer, cherokee and durango...unless you get lucky. Those vehicles are not know for reliability. I 3rd the V8 4runner which is 03+. I have 8 years on my 04 with only a frozen caliper done as a repair. I'm astonished at the reliability. I also tow a 23' supreme w/ 6500lb trailer with it. It's not a Ferrari but it does very well I think. You could find one in the 7-8K range and wouldn't have to dump much much money in it for quite a while, if ever. You will spend a lot of money and or time wrenching on the other vehicles you mention, so budget that in.

How much can you get for the escalade? You might not be much worse off just keeping that.

Good luck finding a V8 4runner for $5k unless it's total piece of shifgsty with a zillion miles on it.
The best abng for your buck hands down is to find essentially the same vehicle you have now except older....get a '90's model tahoe/yukon/suburban.
I have a ton of miles in the seat of all of the big 3 trucks over the last 20years and the 88-98 GM fullsize trucks/suvs are still about the most bulletproof out there.

toyota will run ever. Jeeps too, you can expect about to put about 400K on a 4.0L Jeep engine. The tranny will be shot in about half that. Tons of parts for them and tons of them out there. can be had for about $3k

I've got a 97 tahoe that has a ton of miles, but runs excellent, tows excellent, is SUPER comfy to drive, and really gives me no reason to get rid of it. (since it isn't worth much on a trade or even private sale)

That said, I would tend to disagree with antodio suggesting that if you buy a toyota you are basically golden while you will spend a ton of time fixing the others. I fixed NOTHING on my tahoe that I did buy with about 60k on it...on the other hand, I fixed about a dozen things on the Toyota I bought within about 3 or 4 months of owning it...and it didn't last as long as everyone wants you to believe toyota's last. I've got two friends with trailblazers and none have had any issues with them...

Buying used is a crap shoot no matter what brand you buy. You can get good/bad with either...so keep that in mind. I wonder if you could find someone interested in a trade...? (plus cash type thing)

Your used to V8 power with the escalade, so i would go with a 96-99 Chevy Tahoe or Silverado. I own a 99 2 door and its a machine. LT trim models will come with leather, power seats, G80 limited slip differential, 5.7 vortec V8 providing 330lb-ft of torque at 2800 RPM and a 7,000 pound towing capacity. If your pulling 5k lb or under, 3.42 or 3.73 gears wont make a ton of difference. My tahoe doesn't complain much at all when towing my 08 VLX.

Parts are easy to obtain and are very cheap. Main concern on these trucks is that the intake manifold gaskets have been replaced. If you find a lower mileage one with around 100k, they are suspect for intake manifold leaks thanks to GM's stupid plastic gasket design. I did the repair on my truck 40k ago for around $100 in parts and 10 hours out of my weekend. 172k on my Tahoe and still pulling strong with stock engine and transmission with minimal maintenance.

I had a bit of issues with the escalade but now (knock on wood) everything runs smooth. Of course, if i'm swapping my truck for an older one, and need to throw the difference in repairs, i'ts not worth it.

If i can find a decent, cheap and reliable truck, will 5000lbs towing capacity would be enough for my boat?

you'd be better to sell it than trade it. And then go with a Sub, Tahoe or Yukon bought outright they are undervalued right now. I have a 99 Yukon with 125K on it and have only replaced some power locks and an inside door handle--along with regular maint items. Great tow vehicle.

So you would get the 4runner and 8 grand in exchange for the Escalade? The 4runner is probably worth 5-7k I would assume, depending on condition. What is your escalade worth? 15-18? If your is worth closer to 18 I wouldn't think it would be much of a deal. if you only think yours is worth 15 and the 4runner is worth 7ish it sounds like an even swap. I think the 4 runner should do the trick. I would just make sure hte timing belt and water pump have been replaced. You would save some gas and insurance I am guessing with the 4runner.

I still like the idea of a tahoe or yukon in the mid to late 90's but you won't gain anything really on MPG.

Escalades prices, especially my year range have go down noticeably. (at least here in eastern Canada)
A mint Caddy with low mileage will go at 15-16K TOP! Mine is worth around 12K in this market with the wheels.

I like the Toyota's for their bulletproof reputation, but I'm not sure the capacity of 5000lbs is enough for my needs...

Escalades prices, especially my year range have go down noticeably. (at least here in eastern Canada)
A mint Caddy with low mileage will go at 15-16K TOP! Mine is worth around 12K in this market with the wheels.

I like the Toyota's for their bulletproof reputation, but I'm not sure the capacity of 5000lbs is enough for my needs...

I have a 2008 4Runner with the 4.0 V6. My boat and trailer are 3,500 lbs. dry. My trip to the lake is as short as yours. I have some steep, short grades on the way there. My 4Runner does fine but I have the 4.0 which is a big improvement over the 3.4 and I am towing 1,500 lbs. less. I have access to a F150 for longer trips to the mountains.

Based on my experience you may need to look for a 4Runner with at V-8 for the low end torque if you are going to tow 5K dry. The V8 won't help the short wheel base though. This is what really limits the 4Runner especially on steep down grades.

Jonathan, Check out the dodge durangos. My family has had one since 1999. My dad bought it new to tow a 210 sea ray. I then used it to tow my supra launch. and now it is used to tow a 24 ft pontoon. That thing is a good pulling vehicle and on problem was a transmission at around 80k , it now has 155k. Doesnt get used much but when needed it is ready. We had the one with the 5.9L V8, only made that engine for a few years.

When i towed my supra i only towed about 10 miles and the launch was a mild steepness. I put it in low and it pulled my boat right out. If the ramp was wet i put it in 4 low and it pulled it right out still no slipping.

If you go with a Durango with the 5.9l V-8 do a water pump swap. My last 2 Dodges had the water pump go out at around 65k. Just my experience. You should have plenty of power to tow with the Durango. Still dealing with a short wheel base though.